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Synthesis, Characterization, Evaluation of Interfacial Properties and Antibacterial Activities of Dicarboxylate Anacardic Acid Derivatives from Cashew Nut Shell Liquid of Anacardium occidentale L.
Journal of Surfactants and Detergents ( IF 1.6 ) Pub Date : 2020-01-24 , DOI: 10.1002/jsde.12384
Sonia Koteich Khatib 1, 2 , Johnny Bullón 2 , Jesús Vivas 1 , Ali Bahsas 1 , Yolima Rosales‐Oballos 3 , Ronald Marquez 2 , Ana Forgiarini 2 , Jean Louis Salager 2
Affiliation  

Anacardic acid, 2‐hydroxy‐6‐[(8Z,11Z‐pentadeca‐8,11,14‐trienyl]‐benzoic acid, extracted from cashew nut shell liquid (CNSL), has been structurally modified to obtain the 2‐(O‐carboxymethyl)‐6‐[(8Z,11Z)‐pentadeca‐8,11,14‐trienyl]‐benzoic acid and its disodium carboxylate salt. Our separation method allows to easily obtain anacardic acid, which has been of interest for the fabrication of green products. These methods proposed for the first time to synthesize these derivatives are short and cheap, and with a high yield. The elucidation of its structure was carried out by means of infrared spectroscopy (IR) and nuclear magnetic resonance (NMR) techniques. Interfacial rheology properties of surfactant‐air‐water and surfactant‐heptane‐water systems were determined by using a new oscillating spinning drop rheometer apparatus. Physicochemical characterization was performed with a salinity scan in a surfactant‐heptane‐brine system, obtaining a value of the surfactant characteristic parameter σ = −4.3 for the disodium salt and a critical micellar concentration (cmc) of 0.08 wt%, showing high surface activity. The biological activity of both compounds was determined and measurements of their potential antimicrobial activity against Gram‐positive and Gram‐negative bacteria were performed, exhibiting high effectiveness, especially for the disodium salt against Gram‐positive bacteria.

中文翻译:

西洋参腰果腰果壳液中二羧酸正丁酸衍生物的合成,表征,界面性质和抑菌活性的研究。

从腰果壳液(CNSL)中提取的2-羟基-6-[(8Z,11Z-pentadeca-8,11,14-三烯基]-苯甲酸)对氨基甲酸经过结构化改性以获得2-(O -羧甲基)-6-[((8Z,11Z)-pentadeca-8,11,14-三烯基]-苯甲酸及其羧酸二钠盐。我们的分离方法可轻松获得制卡纳酸,这在制造中很重要首次提出的合成这些衍生物的方法短且便宜,且收率高,通过红外光谱(IR)和核磁共振(NMR)技术对其结构进行了阐明通过使用新型的振荡纺丝滴流变仪,测定了表面活性剂-空气-水和表面活性剂-庚烷-水系统的界面流变性。在表面活性剂-庚烷-盐水系统中通过盐度扫描进行理化表征,获得表面活性剂特征参数的值对于二钠盐而言,σ = -4.3,临界胶束浓度(cmc)为0.08 wt%,显示出很高的表面活性。确定了这两种化合物的生物活性,并对它们对革兰氏阳性菌和革兰氏阴性菌的潜在抗菌活性进行了测定,显示出很高的效力,尤其是对于二钠盐对革兰氏阳性菌而言。
更新日期:2020-01-24
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